Top 20 Best Tours to try in Portland, Oregon

When you’re visiting one of the most unique and beautiful cities in the USA you’ll need to do it justice. One of the best ways is to explore in a thorough, fun and sociable way on an organized tour. From spooky ghost tours to family-friendly days out, here are the best tours to try in Portland, Oregon (in no particular order)...

1. Portland: Two-hour family walking tour – spend a family fun day out on this guided tour

Portland Family Walking Tour

An excellent introduction to the city of Portland, Oregon, and well-suited when you have little ones in tow. This Portland Tour is a gentle walking tour through the downtown neighbourhood, seeing some of the historic sites, sights and landmarks and learning just enough about the history for a flavour of things to do another day.

It’s great for keeping the kids amused by finding the unusual miniature horses dotted around the streets – although everyone loves weird surprises. This tour feels like a lot less than 2 hours.

2. Portland: Flightseeing Tour Mount Hood – take a unique and scenic flight tour

Flightseeing Tour Portland Mount Hood

Very different from the usual tour. This involves a stunning flight in a light aircraft to the east of Portland over the Columbia River Gorge, with far reaching views of the mountains and the Mount Hood National Forest below.

Try to pick a good, clear day so you see the best of the scenery although, even on a not so clear day, you should get to see the Elowah Falls, Horsetail Falls and Multnomah Falls on the descent. All-in-all, an hour well spent.

3. Portland: Food Carts, Pods & Patios Tour – a fun tour for foodies

Food Cart Tour Portland Oregon

A roughly 3-hour small-group walking tour, around the Central Eastside district of Portland, sampling the delights of its food and beverages – what’s not to like? Food carts and trucks are small kiosks that serve single specialities of almost every cuisine imaginable.

This tour samples some of the more interesting carts, ending up at a local craft beer brewery with a huge patio to rest and wash it all down.

4. Portland: Downtown Ghost Tour – a popular tour exploring Portland’s eerie downtown hauntings

Ghost Tour in Portland Oregon

Everyone loves a bit of the unusual or macabre. This 1-hour circular walking tour packs in 8 locations around the dark streets of downtown Portland. Starting and ending at the Lan Su Chinese Garden, you get to hear genuine tales from the city’s gloomy past with eyewitness testimony and, just maybe, you might capture a spook on your camera.

A highlight of the tour is a stopover at the infamous Shanghai Tunnels with their rich history of legal and illegal activity over the last 150 years.

5. From Portland: Columbia Gorge Waterfalls Tour

Columbia Gorge Waterfalls Tour

Go on a private group tour to see the spectacular Columbia River Gorge, Multnomah Falls, Crown Point, Beacon Rock, Bonneville Dam, Bridge of the Gods and thousands of acres of lush, green forest.

A breathtaking and great way to enjoy the beautiful natural scenery of this part of Oregon.

6. Portland: Willamette Valley Character Wineries – visit tasting rooms, wineries, and vineyards

Willamette Valley near Portland

If you’re interested in wine, especially the famous local pinot noir, this is a great tour heading south to visit 3-4 boutique wineries in the Willamette Valley.

Here you’ll get to taste some of the lesser-known estate wines in the spectacular surroundings of this picturesque valley with its unique, almost Mediterranean climate. There’s a good lunch stop at a local farm shop en route – just to drag you away from the wine for a short time.

7. Portland: 2.5 Hour Dinner Cruise Through Downtown – a romantic and scenic tour

Portland Dinner Cruise Tour

This is a wonderful choice for a memorable evening; 2½ hours dining and wining along the Willamette River whilst downtown Portland slowly illuminates and drifts past.

You can simply sit and gaze out of the windows or take a stroll to the observation deck where a narration points out landmarks and places of interest. A refined and relaxing way to enjoy the splendid sights of Portland at dusk.

8. Portland: Columbia Gorge Waterfalls 40-Minute Scenic Flight – embark on a scenic flight through Oregon’s pride and joy

Portland- Columbia Gorge Waterfalls 40-Minute Scenic Flight

One of the best ways to truly appreciate the wildness and grandeur of the Oregon scenery is from the air. This 40-minute flight in a light aircraft passes along the Columbia River Gorge taking in the beautiful waterfalls and forests below.

A top tip is to try and time your flight to capture the superb western sunset on the return journey, which creates an unforgettable sky as the sun sinks into the Pacific.

9. Portland: 2 Hour Champagne Brunch Cruise Through Downtown – romantic lunch and dinner cruising around the Portland waterways

Champagne Brunch Cruise Through Downtown Portland

A very enjoyable, relaxing way to see another side of Portland is with this brunch cruise along the Willamette River. Sip some champagne, nibble some lunch and watch the city pass by with, often, a little live entertainment too.

On a warm day, climb a couple of floors to the observation deck for a narration of the passing sights or, on a wet day, stay at the table with maybe another glass of champagne.

10. From Portland: Northern Oregon Coast Day Trip – a must-do tour from the city

Mount Hood Wine and Waterfalls Full-Day Tour

An excellent comprehensive day tour for a full flavor of the area around Portland. The tour heads east through the Willamette Valley to begin at Mount Hood, the highest peak in Oregon, with its year-round giant pyramid of snow.

This is followed by a local farm-produce lunch and tasting at a winery, then down to the Columbia Valley for more wine tasting and finishing at the beautiful Multnomah Falls. A truly good day out.

11. From Portland: Northern Oregon Coast Day Trip – visit one of the most beautiful places on a day trip from Portland

Northern Oregon Coast Day Trip

For a little more adventure try this trip west to the Pacific coast around the historic town of Tillamook. It’s a full day tour but worth the journey for an opportunity to see the staggeringly beautiful coastal rock formations and beaches of the shoreline.

The tour heads out from Portland along the Tualatin Valley until reaching the ancient forests and giant stacks of the Oregon coast. If the weather is bad, wrap up warm but go anyway, just to witness the Pacific Ocean crashing in full drama against the ancient coastline.

12. Bend: Half-Day Volcano Tour – explore the belly of an ancient volcano

Volcano Tour from Portland Oregon

If you’re in Portland, you might want to think twice about this tour as it’s a good 4-hour drive just to reach Bend. If, however, you’re anywhere near central Oregon this is a definite must-see.

The volcanic lakes high in the ancient volcanic mountains are simply beautiful and the hike to reach them is short and accessible to all. You will be 6,300ft above sea level so wrap up warm and try to pick a clear day to get the very best of the stunning views.

13. Bike Portland: Bridges, Neighborhoods, Poetry, and Roses – one of the best ways to get a full experience of the city

Bike Tour Portland Oregon

This cycling tour is a very enjoyable, relaxed way to spend about 3 hours discovering some of the lesser-known corners of southeast Portland – and not too strenuous as it’s less than 10 miles on flat routes, much of the time following the banks and bridges of the Willamette River.

The guide pauses with occasional stops for gardens, one-of-a-kind markets, art collectives, sculptures, bridge viewpoints, and some secret river beaches. Along the way you can read poetry written on murals, on sidewalks, and carved into rocks.

14. Portland: Smart Phone Scavenger Hunt – a fun way to see the city at your own pace

Smart Phone Scavenger Hunt

A fun way to spend half a day is with this little interactive piece of tech as a guide. The route covers around 2½ miles of places and sights, starting at Pioneer Courthouse Square and winding through the Arts District with clues, views and discoveries along the way.

It’s an interesting way to find out about Portland as you pass landmarks such as the Portland Art Museum, statue of Portlandia, Ira Keller Fountain Park, and Powells Books. Perfect for self-paced; take as much time as you want or, if you’re with a bigger group, split into teams and make it a race!

15. Portland’s Eastside Craft Brewery Walking Tour – tasting beer samples spanning the gamut in style, flavors, and colors

Craft Brewery Walking Tour Portland

Here’s a fabulous opportunity for the beer buffs to spend 2-3 hours legitimately sampling the finest craft ales and ciders, around the industrial waterfront inner Eastside neighbourhood of Portland, Oregon.

The small-group guided tour takes in a range of diverse craft breweries over a couple of miles so you can try a full range of flavours and techniques from the long US history of brewing beer. Top tip for this tour is to take a photo of your favourite tipple and brewery – as you won’t remember in the morning.

16. Portland: Underground Donut Tour – taste Portland’s best donuts

Underground Donut Tour Portland

Just when you thought there weren’t enough doughnuts in the world, along comes a 2-hour tour of 4 top doughnut purveyors in Portland, including priority service at the famous Voodoo Doughnuts in the Old Town.

Savour classics like glazed and chocolate, and discover some more adventurous flavours, like lavender, guava colada, sesame and, frankly, anything that can balance on that small doughy circle. A fun, highly enjoyable, different experience.

17. Discover Portland: Half-Day Small Group City Tour – an awesome way to discover the city

Half-Day Small Group City Tour

An excellent classic-type tour involving a half day being driven to selected famous sites around Portland. The route tours the landmarks and stops at the International Rose Test Garden in Washington Park for a wander and sniff of the incredible fragrances, from over 10,000 varieties, that give Portland the nickname “City of Roses”.

Then up to the historic Pittock Mansion high in the hills overlooking the city for stunning views and beautiful gardens. A perfect, lazy introduction to this beautiful, lush city.

18. Cascade Locks: Columbia Gorge Sunday Brunch Cruise – one of the best and most beautiful tours to take 

Columbia River Gorge Dinner Cruise

A short drive to the east of Portland, up the Columbia River is a wide stretch known as Cascade Locks. This tour takes you aboard a sternwheeler (like a paddle-steamer, but with a huge wheel at the back) to calmly cruise the river and dine on a champagne brunch as the forests and mountains roll by.

On the return trip an onboard narration tells you about the history and landmarks of this beautiful natural waterway. You can sit and admire the view from your table or climb to the wide observation deck for a panoramic experience of this majestic landscape.

19. Portland: Private Multnomah Falls Tour – experience the beauty spot in a unique way

Private Multnomah Falls Tour Portland

The spectacular Multnomah Falls are one of the biggest tourist attractions and a must-see for any tour around Portland, Oregon.

There are several hiking trails that will get you there, or there’s this 30-minute private flight in a light aircraft completely avoiding the crowds and getting a full panoramic view of the scenic waterfalls and forest below. Highly recommended for an unforgettable experience.


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